title: Effect of carbohydrate amino group modifications on the cytotoxicity of glycosylated 2-phenyl-benzo[b]thiophenes and 2-phenyl-benzo[b]furans.
abstract: In previous studies, we have identified a family of benzo[b]furan and benzo[b]thiophene derivatives linked to amino sugars (1-6) that are cytotoxic to a range of cancer cell lines. We describe here an exploration of the effect of structural modification of the amino group on one of the carbohydrate residues (4-amino-2,3,4,6-tetradeoxy-α-l-threo-hexopyranoside) on in vitro cytotoxicity. It has been found that maintaining at least one basic functional group around the C-4 position in the carbohydrate moiety is crucial for cytotoxicity. Furthermore, it appears that modifications around the C-4 position are limited by suitable hydrophilic/hydrophobic and/or ionic interactions, as well as steric constraints.
authors.affiliation: Alberta Ingenuity Centre for Carbohydrate Science and Department of Chemistry, The University of Alberta, Gunning-Lemieux Chemistry Centre, Edmonton, Canada AB T6G 2G2.
authors.forename: Wei
authors.initials: W
authors.lastname: Shi
authors.forename: Todd L
authors.initials: TL
authors.lastname: Lowary
mesh_terms: D000596:Amino Acids / Q000737:chemistry / Q000494:pharmacology*; D000606:Amino Sugars / Q000737:chemistry / Q000494:pharmacology; D001572:Benzofurans / Q000737:chemistry / Q000494:pharmacology*; D002241:Carbohydrates / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D003603:Cytotoxins / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D056945:Hep G2 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019800:Phenol / Q000737:chemistry; D013876:Thiophenes / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000596:Amino Acids; D000606:Amino Sugars; D001572:Benzofurans; D002241:Carbohydrates; D003603:Cytotoxins; D013876:Thiophenes; D019800:Phenol